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US7790654B1 - Plant protection agents - Google Patents

Plant protection agents Download PDF

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Publication number
US7790654B1
US7790654B1 US09/403,192 US40319298A US7790654B1 US 7790654 B1 US7790654 B1 US 7790654B1 US 40319298 A US40319298 A US 40319298A US 7790654 B1 US7790654 B1 US 7790654B1
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United States
Prior art keywords
crop protection
protection composition
composition according
weight
proportion
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Expired - Fee Related
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US09/403,192
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English (en)
Inventor
Jacki Müller
Achim Zöllkau
Vera Pohl
Ewa Bednarska
Rainer Süssmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
STEFES AGRO GmbH
Bayer CropScience Deutschland GmbH
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Bayer CropScience Deutschland GmbH
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Application filed by Bayer CropScience Deutschland GmbH filed Critical Bayer CropScience Deutschland GmbH
Assigned to STEFES AGRO GMBH reassignment STEFES AGRO GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BEDNARSKA, EWA, MULLER, JACKI, POHL, VERA, SUSSMANN. RAINER, ZOLLKAU, ACHIM
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters thereof

Definitions

  • the present invention provides crop protection compositions comprising active compounds having foliar or systemic action which make it possible to widen the activity spectrum and the activity by employing a surfactant/silica gel mixture.
  • crop protection compositions are ready-to-use preparations of active compounds which are directed in particular against animal, microbial or plant pathogens of useful or crop plants.
  • silica gels as so-called “inert” cocomponents in crop protection preparations.
  • the use of silica gels as auxiliaries for preparing dispersible suspensions is described in Bühel “Rooenschutz und Swdlingsbehimmpfungsstoff”, 1977, page 198.
  • Tadros describes the use of silica gels as additives for suspension concentrates to prevent sedimentation and caking.
  • the use of silica gel as filler is described in Foy and Pritchard in “Pesticide Formulation and Adjuvant Technology”, 1996, page 85.
  • mineral oils and vegetable oils and their derivatives and also specific surfactants, for example polysaccharides, ethoxylated triglycerides, ethylene oxide or propylene oxide copolymer adducts with ethylenediamine as central starter unit, polyethoxylated fatty acids and amides thereof and also ethoxylated alkylaryl alcohols having typically 6-10 oxyethylene units are employed here.
  • specific surfactants for example polysaccharides, ethoxylated triglycerides, ethylene oxide or propylene oxide copolymer adducts with ethylenediamine as central starter unit, polyethoxylated fatty acids and amides thereof and also ethoxylated alkylaryl alcohols having typically 6-10 oxyethylene units are employed here.
  • the amount of such additives or bioactivators that is required varies between 100 g/l of ready-to-use preparation to from 2 to 3 l per ha, for example in the case of the mineral and vegetable oils as tank mix partners of the herbicides having foliar action.
  • the concentration of the active compounds can be considerably increased (cf. DE 43 29 974). These advantages reduce, for example, packaging, transport and also storage costs considerably.
  • the simultaneous use of the inorganic adsorbents selected according to the invention preferably the use of silicic acid, alumosilicates and/or aluminium oxides in combination with specific surfactants in powders, granules and aqueous suspension concentrates of active compounds having foliar or systemic action resulted in an unexpected increase in the activity potential and in a widening of, in particular, the weed application spectrum, compared with conventionally formulated emulsion preparations and suspension concentrates.
  • FIG. 1 shows the correlation of activity (%) and silica gel content (g/l) for a phenmedipham/desmedipham (PMP/DMP) suspension concentrate mixture.
  • FIG. 2 illustrates a comparison of activity of two crop protection compositions in various plant species.
  • FIG. 3 shows a comparison of activity of the crop protection compositions at different application rates.
  • the silicic acid used can be colloidal silicic acid, generally referred to as silica gel, but also the so-called pyrogenic silicic acid, generally referred to as Aerosil. Aluminium oxide in all its modifications and hydrated forms and alumosilicates, in particular the specific surfactants selected according to the invention likewise exhibited a surprising activity-increasing effect and resulted in a widening of the application spectrum. Preference is given to using silica gel.
  • the inorganic adsorbents selected according to the invention can be added in proportions of from 0.5 to 25.0% by weight, preferably in proportions of from 2.0 to 15.0% by weight, to the novel crop protection compositions according to the invention.
  • the surfactants to be employed according to the invention are selected from the group of ethoxylated C 6 to C 20 alcohols, preferably C 6 -C 16 , of the ethylene/propylene oxide block copolymers, if appropriate comprising ethylene diamine as starter unit, and of the alkyl ether sulphates and their combinations. It is also possible to employ ethoxylated castor oil. Preference is given to using ethoxylated tridecanols having from 5 to 13 ethylene oxide units, sodium, potassium or ammonium alkyl ether sulphates, in particular sodium, potassium or ammonium fatty alcohol diglycol ether sulphates or mixtures of these surfactants.
  • the proportion of surfactant in the crop protection compositions according to the invention is from 5.0 to 40.0% by weight, preferably between 10.0 and 25% by weight.
  • the sum of the proportions of adsorbents selected according to the invention and surfactants selected according to the invention is from 5.5 to 45.0% by weight, preferably from 15.0 to 25.0% by weight.
  • the novel crop protection compositions according to the invention comprise herbicides which have both foliar action and soil and foliar action from the groups of the urea derivatives, the carbamates, biscarbamates, diphenyl ethers, pyridolylacetic acid derivatives, pyridazines, triazines, triazinones, uracils, sulphonylureas, benzofuran derivatives and also glufosinate and glyphosate, and their salts or esters, and also mixtures of some selected active compounds.
  • PMP phenmedipham
  • DMP desmedipham
  • metamitron and/or ethofumesate.
  • Suitable fungicidally active compounds are morpholines, azols, phthalimides or piperidines, suitable insecticides are pyrethroids, carbamates or organophosphates, and the possible salts or esters and also mixtures of selected abovementioned active compounds.
  • the proportion of active compound in the crop protection compositions according to the invention is from 5.0 to 75.0% by weight, preferably from 15.0 to 55.0% by weight.
  • the crop protection composition according to the invention may comprise auxiliaries and/or carriers known per se which are customarily used for suspension concentrates.
  • Antifreeze agents, stabilizers, antifoams, wetting agents and dispersants and also, if appropriate, other fillers may be mentioned by way of example.
  • the wetting agent and dispersant can be selected, for example, from the groups of the phosphated di- or tristyrenephenol ethoxylates in the phosphate form and/or of the lignin sulphonates.
  • the crop protection compositions according to the invention are prepared by processes known per se, for example the wet milling principle. To this end, the individual components (active compounds and auxiliaries) are finely ground with an appropriate amount of water in a suitable apparatus, for example a bead mill.
  • the components are preferably adjusted to a degree of fineness of from 0.5 to 20 ⁇ m, in particular to a degree of fineness of ⁇ 10 ⁇ m.
  • a degree of fineness of from 0.5 to 20 ⁇ m, in particular to a degree of fineness of ⁇ 10 ⁇ m.
  • solid preparations granules or powders
  • use is likewise made of methods corresponding to the prior art.
  • the crop protection compositions according to the invention exhibit, in addition to the known toxicological and ecotoxicological advantages, surprisingly an additionally increased biological potential in the control of weeds which as yet has not been able to be controlled using equivalent application rates of known preparations.
  • compositions prepared using the adsorbent/surfactant combination according to the invention make it possible for the first time to employ crop protection agents from the group of the carbamates and biscarbamates for controlling camomile species, for example Matricaria chamomilla (MATCH) and Matricaria inodora (MATIN).
  • camomile species for example Matricaria chamomilla (MATCH) and Matricaria inodora (MATIN).
  • MATCH Matricaria chamomilla
  • MATIN Matricaria inodora
  • the table shows the scores obtained in a herbicide trial in sugar beet.
  • Suspension concentrate A g/l desmedipham 160 phenmedipham 160 Soprophor FL 60 25 Volpo T/7 85 100 Genapol LRO 30
  • Tensiofix LX Spezial 5 silica gel SM 614 40 antifreeze agent 40 stabilizer 1 antifoam 5 water ad 1 l
  • Suspension concentrate C g/l desmedipham 320 Soprophor FL 30 Volpo T/7 85 135 Genapol LRO paste 15
  • Suspension concentrate D g/l phenmedipham 320 Soprophor FL 60 45 Volpo T/10 120 Genapol LRO 45 Tensiofix LX Spezial 5 silica gel SM 614 45 antifreeze agent 40 stabilizer 1.0 antifoam 7 water ad 1 1 antifreeze agent 40 stabilizer 1.0 antifoam 7 water ad 1 l
  • Suspension concentrate E g/l metamitron 550 Hoechst LFS 35 Genapol LRO 40 Volpo T/10 120 silica gel Tixosil 38A 37 antifreeze agent 35 antifoam 5 stabilizers 1 water ad 1 l.
  • a crop protection composition according to the invention (suspension concentrate C; SC C) which comprised 320 g/l of desmedipham was compared with a crop protection composition known from the prior art (Betanal® AM from Hoechst Schering AgrEvo GmbH; Betanal AM comprises only desmedipham; EC), which comprised 160 g of desmedipham/l. 0.75 ml of the suspension concentrate according to the invention (SC C)/ha and 1.5 l of Betanal AM (EC)/ha were applied (this corresponds to equivalent amounts/ha). The results are shown in Tab. 3 and FIG. 2 .
  • the substantially improved activity of the crop protection compositions according to the invention becomes evident when the relative fresh weights of the weeds are compared.
  • the suspension A according to the invention (SC A) was compared with Betanal® AM 11 from AgrEvo which comprised DMP and PMP in a ratio of 1:1.
  • Fresh weight is defined as the mass of the above-ground parts of the plants.
  • Table 4 and FIG. 3 The results are shown in Table 4 and FIG. 3 .
  • Example 4 shows a comparison of the activity of approved emulsion concentrates (Betanal AM and Betanal AM 11) with suspension concentrate according to the invention having a proportion of silica gel of 40 g/l or 20 g/l at different application rates. Both the integral (6 species) and the species-specific activity is substantially increased when the composition according to the invention is employed.
  • Table 7 below states the type and group association of the cocomponents used.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Toxicology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Investigating Or Analyzing Materials By The Use Of Fluid Adsorption Or Reactions (AREA)
  • Pretreatment Of Seeds And Plants (AREA)
US09/403,192 1997-04-15 1998-03-31 Plant protection agents Expired - Fee Related US7790654B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19715639 1997-04-15
PCT/EP1998/001870 WO1998046075A1 (fr) 1997-04-15 1998-03-31 Produits phytosanitaires

Publications (1)

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US7790654B1 true US7790654B1 (en) 2010-09-07

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US (1) US7790654B1 (fr)
EP (1) EP0975215B1 (fr)
JP (1) JP3849040B2 (fr)
KR (1) KR100459093B1 (fr)
CN (1) CN1195409C (fr)
AT (1) ATE222693T1 (fr)
AU (1) AU731215B2 (fr)
BG (1) BG64685B1 (fr)
BR (1) BR9809095B1 (fr)
CA (1) CA2287180C (fr)
CZ (1) CZ300186B6 (fr)
DE (2) DE19814092A1 (fr)
DK (1) DK0975215T3 (fr)
ES (1) ES2184257T3 (fr)
HU (1) HU229499B1 (fr)
NO (1) NO323297B1 (fr)
NZ (1) NZ338080A (fr)
PL (1) PL195699B1 (fr)
PT (1) PT975215E (fr)
RU (1) RU2212794C2 (fr)
SK (1) SK286000B6 (fr)
TR (1) TR199902419T2 (fr)
UA (1) UA52738C2 (fr)
WO (1) WO1998046075A1 (fr)
YU (1) YU52699A (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE59804901D1 (de) * 1997-06-04 2002-08-29 Basf Ag Fungizide mischung
KR100338621B1 (ko) * 2000-01-24 2002-05-30 전광술 제초제 및 그 제조방법
FR2806878A1 (fr) * 2000-03-30 2001-10-05 Aventis Cropscience Sa Nouveau concentre fluidifiable monophasique comme composition pesticide et/ou regulatrice de croissance
DE10029169A1 (de) * 2000-06-19 2002-01-03 Aventis Cropscience Gmbh Herbizide Mittel
FR2837066B1 (fr) * 2002-03-14 2004-07-16 Michel Gentet Composition phytosanitaire comprenant un principe actif et un compose pulverulent et application a la lutte notamment contre metcalfa pruinosa
KR101002570B1 (ko) 2008-07-08 2010-12-20 아이엠팜(주) 기능성 사과 재배를 위한 베타카로틴 조성물
KR102057445B1 (ko) * 2018-03-06 2020-01-14 주식회사 팜한농 피리미딘다이온계 화합물을 포함하는 제초제 조성물

Citations (9)

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DE42948C (de) F. WILHELM in Herford a. Rh Mischventil für einen kombinirten Gas- und Petroleum-Motor
US4185992A (en) * 1977-03-04 1980-01-29 May & Baker Limited Imidazole derivatives
JPS6323804A (ja) * 1986-07-16 1988-02-01 Mitsui Toatsu Chem Inc 混合除草剤
GB2245494A (en) * 1990-07-06 1992-01-08 Bayer Ag Herbicidal agents based on metamitron/ethofumesate/phenmedipham/desmedipham.
DE4029304A1 (de) 1990-09-15 1992-03-19 Hoechst Ag Synergistische herbizide mittel
DE4329974A1 (de) 1993-09-04 1995-03-09 Stefes Pflanzenschutz Gmbh Wäßrige herbizide Suspensionskonzentrate
WO1995018531A1 (fr) 1994-01-10 1995-07-13 Ciba-Geigy Ag Formulations de poudre mouillable pour herbicides
WO1996003871A1 (fr) 1994-08-03 1996-02-15 Zeneca Limited Formulation de gel
US5658851A (en) * 1993-10-13 1997-08-19 Osi Specialties, Inc. Lipophilic siloxanes as adjuvants for agriculture

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ZA715842B (en) * 1970-09-18 1972-12-27 Fisons Ltd Herbicide
GB1306008A (fr) * 1971-05-24 1973-02-07
US4411692A (en) * 1981-03-26 1983-10-25 Monsanto Company Flowable herbicides
FR2644036B1 (fr) * 1989-03-07 1992-01-17 Rhone Poulenc Agrochimie Combine herbicide constitue d'un emballage polymere hydrosoluble et d'un herbicide contenant de la n-phosphonomethylglycine
DE4319263A1 (de) * 1992-07-03 1994-01-05 Schoenherr Joerg Pflanzenbehandlungsmittel
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DE42948C (de) F. WILHELM in Herford a. Rh Mischventil für einen kombinirten Gas- und Petroleum-Motor
US4185992A (en) * 1977-03-04 1980-01-29 May & Baker Limited Imidazole derivatives
JPS6323804A (ja) * 1986-07-16 1988-02-01 Mitsui Toatsu Chem Inc 混合除草剤
GB2245494A (en) * 1990-07-06 1992-01-08 Bayer Ag Herbicidal agents based on metamitron/ethofumesate/phenmedipham/desmedipham.
EP0465899B1 (fr) 1990-07-06 1995-08-16 Bayer Ag Agent herbicide à base d'une combinaison de métamitron/éthofumésate/phenmédipham/desmédipham
DE4029304A1 (de) 1990-09-15 1992-03-19 Hoechst Ag Synergistische herbizide mittel
DE4329974A1 (de) 1993-09-04 1995-03-09 Stefes Pflanzenschutz Gmbh Wäßrige herbizide Suspensionskonzentrate
US5658851A (en) * 1993-10-13 1997-08-19 Osi Specialties, Inc. Lipophilic siloxanes as adjuvants for agriculture
WO1995018531A1 (fr) 1994-01-10 1995-07-13 Ciba-Geigy Ag Formulations de poudre mouillable pour herbicides
US6656883B1 (en) 1994-01-10 2003-12-02 Syngenta Investment Corp. Wettable powder formulations of herbicides
WO1996003871A1 (fr) 1994-08-03 1996-02-15 Zeneca Limited Formulation de gel
US6436439B1 (en) 1994-08-03 2002-08-20 Syngenta Limited Gel formulation

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Title
Büchel, K.H., "Pfianzenschutz and Schädlingsbekämpfung", Georg Thieme Verlag Stuttgart, p. 198 (1977).
Flabe, Dr. , Jürgen, "Römpp Chemie Lexikon", Georg Thieme Verlag Stuttgart, pp. 2233-2234.
Foy. Chester L., "Pesticide Formulation and Adjuvant Technology", CRC Press, p. 85.
Tadros, Tharwat F., "Surfactants in Agrochemicals", Marcel Dekker, Inc., p. 155.

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DE19814092A1 (de) 1998-10-22
NZ338080A (en) 2000-12-22
BG103804A (en) 2000-07-31
ATE222693T1 (de) 2002-09-15
NO994752D0 (no) 1999-09-29
PL195699B1 (pl) 2007-10-31
NO994752L (no) 1999-09-29
SK286000B6 (sk) 2008-01-07
RU2212794C2 (ru) 2003-09-27
CZ365099A3 (cs) 2000-04-12
JP3849040B2 (ja) 2006-11-22
AU7333798A (en) 1998-11-11
DE59805319D1 (de) 2002-10-02
CN1252688A (zh) 2000-05-10
DK0975215T3 (da) 2002-12-23
AU731215B2 (en) 2001-03-29
HUP0001657A2 (hu) 2000-08-28
TR199902419T2 (xx) 2000-01-21
HU229499B1 (en) 2014-01-28
CA2287180C (fr) 2006-12-05
EP0975215A1 (fr) 2000-02-02
JP2001518903A (ja) 2001-10-16
BG64685B1 (bg) 2005-12-30
KR20010006391A (ko) 2001-01-26
SK142199A3 (en) 2000-06-12
CZ300186B6 (cs) 2009-03-11
BR9809095A (pt) 2000-08-01
KR100459093B1 (ko) 2004-12-03
PL336228A1 (en) 2000-06-19
BR9809095B1 (pt) 2011-06-28
NO323297B1 (no) 2007-03-05
WO1998046075A1 (fr) 1998-10-22
YU52699A (sh) 2001-03-07
CA2287180A1 (fr) 1998-10-22
HUP0001657A3 (en) 2002-03-28
EP0975215B1 (fr) 2002-08-28
PT975215E (pt) 2003-01-31
CN1195409C (zh) 2005-04-06
ES2184257T3 (es) 2003-04-01
UA52738C2 (uk) 2003-01-15

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